Niccolò di Pitigliano

Niccolò Orsini, Conte di Pitigliano (1442-January 1510) was the Captain-General of Venice during La Serenissima's war against the League of Cambrai in 1508-1510. He was also the Field Marshal of the Republic of the Republic of Florence, a title which he gained in 1473. A condotierro, he was a member of the House of Orsini through his mother and father.

Biography
Niccolò di Pitigliano was born in central Italy's Maremma region in Pitigliano, descended from two different branches of the House of Orsini. Niccolo and his father Aldobrandino II of Pitigliano served as condotierri, fighting for Florence (1473, 1485), Siena, the Kingdom of Naples (1463 and 1481) the Papal States (1458, 1482, and 1489), and La Serenissima (Venice, 1495). His contract with Venice lasted for the rest of his life, and in 1508 he was made Captain-General of Venice during the War of the League of Cambrai. Pitigliano faced France, Spain, the Holy Roman Empire, and the Papal States as enemies.

On 14 May 1509, Pitigliano and his cousin Bartolomeo d'Alviano fought the French army at the Battle of Agnadello. Pitigliano escaped the destruction of his army with many of his mercenaries, who soon deserted in droves after it became common news that d'Alviano was captured. Pope Julius II excommunicated every Venetian civilian and seized Ravenna with help from Ferraran troops (the Duke of Ferrara seized the Polesine region for himself), also invading Romagna. In November 1509 Pitigliano took Vicenza, Este, Feltre, and Belluno from the Imperial forces and Maximilian I of Germany failed to capture Padua.

By 1510, Niccolò had settled in a manor in Lonigo, but the people of the community saw him as more of an "old soldier who had outlived his glory." In this time, Niccolò took to drinking and whoring, as well as boasting of his military exploits; earning the distaste of his townsmen. Niccolò often made luxurious purchases in the markets, and walked the streets with courtesans on each arm, using them to feel young, while they in turn used him to feel powerful. Not even his own guards respected him, mocking their master while they were off duty. However, Niccolò nevertheless had several allies – among them, local politicians and clergy who covered up his misdeeds – which he entertained at his manor.

Pitigliano's downfall came in 1510 when a crowd of people began to riot outside of his manor, harboring ill will for him. Pitigiliano was mortally wounded by painter Francesco Vecellio on the rooftop of his house, but he survived. Pitigliano attempted to escape to another town, but died on the way of his wounds.